Think of your car a bit like a fresh Rubber Band. When you first pull it out, it does its job just fine, but the rubber is probably just a little stiff, so it won't be able to do as much as an "older" rubber band.
When you start using it, the rubber starts to stretch, and it begins to assume that stretched shape a little bit more naturally. It'll be slightly bigger than your fresh rubber band, and will be able to hold slightly more.
However, as you use that rubber band more and more, it will eventually wear out too much. That would be the point where it ceases to contract or just outright breaks.
That's mostly how the cars work (as an analogy, not as a comparison). When you first buy the car, you need to work it in a little bit. The oil quality, more or less, determines how much of the car's available power can be used. For the first hundred miles or so of an oil change, you'll have all the power your car is able to use. During this time, it's also being broken in, so the power available is gradually going up.
When the oil starts to fade, you start losing "available" power, but you might still be breaking the car in. So while it may appear that your HP has dropped slightly, changing the oil and bringing it back to that 100% mark will give you back all available power, including the extra power from breaking the car in. That's where your jump in power comes from.
Of course, as you keep driving, you're going to wear out the engine and the available power will begin going back down. This takes a lot longer. When you change the engine, you'll be put near that "fresh" point, but not the whole way there.
With what you're experiencing, it seems like your "break in" period is a bit longer than you might expect. It may also be because you (or your Bobs) are becoming more skilled as drivers. Your Bobs will definitely show some gradual improvement as they level up, but if you're driving the same Endurance Race over and over in the same car, or even different ones but in the same car, you'll begin to learn what you can or can't do, and that might account for some of these changes as well.
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Wow, wall of text. Sorry.